John P. Joy was the proprietor of London House, an eatery on Water Street in Charlottetown. and in 1898 he told the Hillsboro Boating Club that he would donate the “Joy Challenge Cup” for first class sailboat racing in Charlottetown. Dennis O’Mera Reddin offered a cup and medal for second class boats and suddenly there was enough for a regatta. As was common with many trophies the Joy Cup was to be permanently awarded only after being won by the same boat three times.
The first race came off as scheduled on Saturday, 10 September 1898. The two classes were established by length; those under eighteen and those between eighteen and twenty-four feet. It should be noted that the boats racing were not all “yachts” but rather were, for the most part, working boats with lobstermen and fishermen as captains. Following is the account of the race:
The boats entered were owned by Messrs. Taylor, St. Peter’s Island; Hyndman, Lowrie, Crossman, P.P. Gillis, John Mills and League of the Cross, Charlottetown; Robinson, Judson and Jordan, Pownal.
Dr. S.R. Jenkins and Mr. D. O’M, Reddin started the boats from a line stretching from Connolly’s Wharf to a schooner some distance away. The sails were hoisted after the starting signals were given. The breeze was favorable. Mr. J. McCarey was judge of the course and with quite a party of friends watched the course from aboard the Wm. Aitken. The large boats were started at 1:35 p.m. The race was three rounds over a six mile course. Capt. Lowrie’s boat, sailed with great efficiency by James Hughes, held the lead until the last round when she was passed by Robinson’s boat. When within five miles of the finish a heavy northwest squall struck the boats and they were all obliged to lower their sails. Robinson’s boat, after reefing kept onward and was the only one of that class to finish within the time limits. The others had either dropped out of the race during the squall or lost the [time] limit. In the smaller class P.P. Gillis’ boat led until she met with a mishap. Judsons’s and Mill’s boats got through the squall within the time limit. The former led but in consequence of a protest was ruled out for having been over the prescribed length. The Reddin cup was then awarded to Mr. Mills. It now graces the window of Mr. W.F. Carter’s restaurant where the owner may view it with a smile while about his daily avocations.
A second race took place on 27 September after having been postponed for a day owing to light winds. Earlier the committee had published the course and rules in the Guardian. The route was clockwise around the harbour from the committee boat to the buoy off the railway wharf, to the red buoy off Brickmakers [now Battery] Point, thence round the buoy off Rocky Point wharf, to the red buoy at North River and back to the committee boat twice around. The rules of the race are remarkably similar to rules still in use more than a century later.
Although we think of them as a recent development spinnakers and flying sails were in use in light winds. When the boats had completed the course two Captains Taylor from St. Peter’s Island had taken first and second in the large boat category. Capt. James Taylor’s “Report” beat Capt. Dan Taylor in “Pathfinder”. The Taylors operated a large lobster fishing operation and cannery on St. Peter’s Island. In the 2nd class P.P. Gillis “Flirt” led throughout the race but was disqualified at the last buoy and the “Veda” under command of Capt. Mills took first place.